Swirly Cinnamon Chocolate Rolls with Whiskey Vanilla Cinnamon Buttercream Glaze

These chocolatey rolls are a such a decadent treat

that it's hard to eat just one.

Oh Yeah. They're good.

This recipe is an edited version of the recipe first posted in December of 2017 that was also published in our local digital news source, The Washington County Insider. You might enjoy reading what Christmas was like at the Farmhouse that year. Needless to say, we still have little guests who bat their long eyelashes at us once in a while; we live in a farmhouse after all.

There is nothing like the early morning scent of cinnamon and chocolate to greet you as you wake, and this Christmas the house smelled of that yeasty goodness already at 6:00AM. I couldn't wait to make them.

 

Swirly Chocolate Cinnamon rolls with Whiskey Vanilla Buttercream Glaze

Try them and let me know what you think; they take some time, but really are not difficult to make and are worth the trouble. Trust me on this.
This recipe makes about 24 rolls, so plan to make them when you're expecting a crowd, or make ahead and freeze in smaller packets for a month of Sunday mornings. Or just make half the recipe.

Equipment you'll need:  A large mixing bowl, a whisk, a wooden spoon (or use what you've got!), a towel, parchment paper, and large baking sheet or two 13"X9" pans. Measuring cups and spoons, a table knife, and a smaller bowl to mix the filling and then the glaze.
Time to create: Overall, about 3 hours, but each step is done in just a few minutes and then the dough rests. Just stick around the house so you can check up on things every once in a while and can move things to the next step when ready.
Time to bake:  20-25 minutes at 400 degrees F / 200 degrees C.

What you’ll need to make them really tasty:

For the sweet roll dough:

1 T. active dry yeast

4-5 cups of flour, plus more for dusting I like to use King Arthur bread flour; 1 cup = 120gms. However, don't get too worried about measuring the flour.

As you'll see in the instructions, you'll add the flour until the dough looks and feels "right." No worries!

2 c. milk

4 T. butter

¼ c. sugar

1 T. salt

2 eggs

For the filling:

1 1/2 c. sugar

1/2 c. unsweetened cocoa powder

2 t. cinnamon

1 t. espresso powder (optional – the espresso makes the chocolate flavor pop!)

4 t. melted butter

For the frosting:

4 c. powdered sugar

1 t. cinnamon

2 T. Whiskey or whiskey vanilla …. Or just plain old vanilla….  This amount seems like a lot, but you'll get the whiskey flavor coming through in the glaze. If you use plain vanilla, decrease the amount to 2 t. and add just a bit more of the milk

2-3 T. (plus a little more) milk or cream or half & half -or even buttermilk, if you'd like a little tang in your glaze

2 T. softened butter

Here we go:

1. Make the sweet roll dough: Heat the milk and butter in a saucepan over low/medium heat until just a little too warm to the touch and the butter is melted. You might find it helpful to remove the pan from the heat as the butter melts in the warmed milk. Alternatively you can heat the milk and butter in the microwave.
2. Place the yeast and about 2 cups of the flour into a large mixing bowl, add the sugar and salt and stir together with a wire whisk.
3. Pour in the warm milk and melted butter and beat the mixture with the whisk until well blended. Add the eggs and beat it again for about a minute, or until the eggs are blended in well and the mixture looks slightly bubbly. Give it an extra whip around with that whisk for good measure. This mixture should be very well blended and you should see a few bubbles form as you finish whisking.
4. Add 1 cup of the remaining flour, stirring it in with a wooden spoon- then add more flour, about a half-cup, just enough to create a shaggy, sticky mass of dough. Some of the dough will be sticky and in some areas the flour will not be completely incorporated. Sprinkle a little more flour over the top, cover the bowl with a towel, and let it rest for about ½ hour to allow the flour to absorb some of the moisture from the dough.
5. After about 30 minutes, scrape the sides of the bowl with the wooden spoon to loosen it. Sprinkle several Tablespoons flour on the dough and begin to knead it right in the bowl, adding dustings of flour to keep the dough from really sticking to your hands or the sides of the bowl. Knead about 5-7 minutes, until the dough is soft and slightly sticky, but is also smooth and lightly dimpled.
6. Place the dough in a greased bowl, cover with a towel and allow to rise until doubled in size – about 1 hour. It may take longer if your kitchen is a little cool.

1. Make the pretty rolls: Once the dough has risen, punch it down to release air bubbles, divide it in half and place one of the halves on a flour-dusted board or dough cloth. Roll into a flat rectangle about 1/8 inch thick with a rolling pin.
2. While the dough was rising, you were of course mixing up the ingredients of the filling so it would be ready when you are – which is right now! Make the filling: Place all the filling ingredients into a small bowl and mix thoroughly. The filling will be like a thick paste and you'll find it easier to use your hands to crumble half the filling onto the rolled out dough, dispersing it evenly and using the warmth of your hands to gently press it into the dough. Don't worry if it doesn't completely cover the dough as it will spread as it bakes.
3. Starting on the longer side of the rectangle, roll the dough tightly to create a log. Pinch the opposite side to the main log to keep it from unrolling and gently turn the log over so the seam is underneath. Now, you can cut it into 1 ½ inch pieces with a knife,or you can use my little trick of sliding a long piece of dental floss under the log at the point you wish to cut and cross the ends of the floss tightly together to swiftly cut the log into round, swirly slices.
4. Place the slices cut side down (and up!) on parchment in a large baking pan with sides. Do the same with the remaining half of that dough. Cover the pans with a towel and allow the rolls to rise for another hour until doubled.
5. Bake at 400 degrees F. / 200 degrees C. for about 20 minutes or until lightly golden brown. If they brown very quickly, cover with foil part way through the baking time.

Allow to cool completely, then add the glaze.

Whiskey Vanilla Cinnamon Buttercream Glaze

Place all the ingredients except the softened butter into a medium-sized mixing bowl. Stir until the sugar and the liquids create a thick paste. If the ingredients seem too dry, add more whiskey vanilla to the bowl ½ t. at a time, stirring the thick mixture until it creates that stiff paste. Add the butter and work it into the stiffened paste, then stir it quickly to create a smooth buttercream frosting. Once the buttercream has been made, thin it a little with milk, cream, or buttermilk to make a glaze of about the consistency that you see in the video above. Glaze the rolls and enjoy!

Yum.

How to make Whiskey Vanilla:

Ingredients:

1 vanilla bean for every half-liter of whiskey (or other alcohol, such as vodka) You can reuse beans; just refill the container with whiskey and allow to steep for several weeks. Always add more beans when you top up the whiskey.

I like to make this in a canning jar, then decant to a pretty bottle when ready. You can make it right in the whiskey bottle if you'd like.

Split the vanilla bean(s) lengthwise and scrape out the seeds. Place the bean(s) into the whiskey, replace the cover, and shake vigorously. Allow the bottle to sit on the counter - more to remind you to give it a good shake every day than anything else - and shake it daily for about three weeks. Decant to a pretty bottle. The vanilla makes a wonderful gift, and is used as you would use commercial vanilla extract in baking and cooking.